Dress Up
by HeathenVampires
Summary: "You're all man Dean, I just want to see." Dean has a secret kink, Sam likes it and Cas wants to watch. Wincestiel two shot - now with Dress Up Cas!
1. Dean

**I did say I hate people who request/focus solely on top!Dean because he's 'the manliest', implying bottoming is in some way emasculating. But, of course someone did it anyway.**

 **So rather than name and shame or respond with rude messages, I wrote this.**

 **Don't own the characters - just thoroughly corrupt them. Established Sam/Dean relationship.**

 **Warnings for double penetration, cross dressing, wincest, group and all that fun stuff.**

 **On we go!**

-SPN-

Dean may mock him for being "too tall", but Sam knew his brother loved his long, lean body. Especially at times like this, endless legs wrapped tight around Deans waist as he thrusted into Sam harder, faster, chasing the peak of pleasure they could only find in each other. "Dean, please" Sam didn't even know what he was begging for, tightening his muscular thighs around Dean and moving his hips in sync, desperately seeking release. His brother took pity on the writhing form, reaching a rough, calloused hand down to stroke Sam's cock, hypersensitive with the climax he could feel just out of reach. "Come on baby brother, come for me." The 'pet name' always had the same effect, pushing Sam to crest the wave before crashing over, coming on himself and arching as he groaned in pleasure. It was rare for one to come without the other following, and Sam whimpered slightly as Dean spurted, hot and thick as his cock swelled and twitched with orgasm.

There was always an edge of discomfort as Dean pulled out, but warm and sated in his afterglow, Sam barely noticed as Dean dropped down heavily next to him. "You just get better every time baby brother." Sam was about to answer with something equally witty, but all that came out was a shriek of surprise as the motel room suddenly contained a slightly confused looking angel. "Damnit Cas, do angels have no sense of privacy?" Given that Cas was staring intently at their naked bodies without even indicating he had heard Dean, Sam doubted it. "While I don't condemn any sexual orientation between consenting adults, I don't understand the goal. You two cannot produce offspring, though as you are related that would be unfavorable regardless. Why do humans mate if not for procreation?" Dean grunted, tugging on boxer shorts and moving to the fridge for a beer - apparently unaware or uncaring of the ejaculate Sam had shot over his torso. Shuffling upright awkwardly, Sam bolted for the shower - Dean could give Cas the birds and bees talk since he was the one who had corrupted the angel to begin with. Team Free Will and all that.

By the time he got out of a surprisingly hot shower - it was a kind of roulette in motels - Dean had given a vague, vulgar description that had Castiel looking a little more lost than usual. "So it's not mating, it's sexual intercourse and it produces pleasurable sensations?" "That's right Cas." This was not a conversation Sam wanted to have with anyone, let alone an angel of heaven. Taking the beer Dean offered, Sam sat down on the edge of his bed and drank deeply, trying to mask the mounting anxiety that Cas was about to freak out about two brothers having a lot of sex with each other. Theexpected freak out didn't come, a kind of intense silence filling the room for a few minutes. "So if two male humans mate, sorry, have sexual intercourse, which one is the female equivalent?" Smirking knowingly at Dean, Sam tried to correct Cas. "Neither. If we wanted a female, we would find one. We are both all male in the relationship, regardless of who tops that night."

Dean was a little more crude, smiling in a way that was both open and seductive as he wiggled his eyebrows suggestively. "I don't bang Sammy cus I can't get a girl, it's just so much better with a guy. Plus, he bangs me good and hard too." Hoping Dean didn't shoot him, purely for the look of surprise on the angels face, Sam drained his beer and wiped his mouth before adding "Dean likes to be a girl for me sometimes." Castiel did indeed look perplexed, and Dean looked like he was seriously contemplating pulling his gun out. "Seriously Sam? You gonna start shouting about that?" Smiling unapologetically, Sam shrugged. "He could have landed in here when you were wearing a pretty skirt and blowing me with that cute pink lip gloss on anyway." "I don't understand. I thought neither of you were female."

"We aren't Cas, but some people like to play dress up. Dean happens to be one of them. Though he might shoot me now so I'll never see him sitting pretty again." Cas looked between them, cocking his head and clearly trying to work something out. "Can you show me? I think this is one of those things I require demonstration of." "An angel of the Lord wants to watch me get fucked by my brother?" "Is that something I shouldn't want?" Chuckling at Castiels innocent eyes, Sam looked to Dean. "I'm game if you are big brother." "You know me. Always down to break the rules." Sam could already feel his cock twitching in interest, Dean's boxers beginning to tent under the motel table. "Better choose your outfit then." Dean scowled, but there was a smirk at the edges so Sam reclined on the bed, his posture screaming "I'm waiting". Dean drained the last of his beer, standing up and nobody could have missed Cas looking at the rising erection with wide eyes.

"That's nothing angel, wait for the real show." Cas swallowed heavily, no words leaving his slightly open mouth. If Sam didn't know better, he would say the angel was aroused. Shaking the thought away, he watched as Dean rooted through his duffel bag before disappearing into the singing through his nerves, Sam squeezed at his erection as he listened to Dean "getting ready". He knew all the sounds by now, the ping of elastic where Dean pulled on lace panties, the zipper where he did up the dress (finding one to fit for a 'bachelor party' had been fun), the sound of lip gloss and mascara being opened. The last sound, a click, confused him but he figured he would know when Dean came back out. Cas was watching the door himself, no doubt wondering what would come back out. The first time Dean had put makeup on was as a joke, letting one of the daughters of their various babysitters as teenagers "play" - an already seasoned hunter at the mercy of a nine year old girl had stayed with Sam forever. He had thought little more of it, going off to college and losing touch with the family.

When Dean came back for him, pulling him into true Winchester life again, Sam had all but forgotten that time until he returned early from a girls house, liking her less and less as the alcohol he had drunk wore off. He still remembered Dean's yelp, bending down in the sink to scrub at his face - he hadn't even closed the bathroom door. Spotting the makeup tubes on the bathroom side, Sam put two and two together. "Dean, were you putting makeup on?" "No! What on earth would I do that for?" Sam had shrugged, popping open a beer and taking a long gulp. "I don't know, you might like it?" Eventually, Dean admitted he did like it, but nobody was allowed to know because he didn't want to be a laughing stock, and their father would never understand. Nodding in agreement, Sam never brought it up again. Until their father had died, the mindless grief somehow ending in Sam and Dean falling into bed together, taking turns pounding out frustration and loss into each other until they were both bruised and drained and sore.

They had avoided each other for a couple of hours, and Dean was halfway to alcohol poisoning by the time Sam returned to their motel room. "Sammy..." Dean didn't get any further before bolting into the bathroom, throwing up and almost passing out. Used to this on occasion, Sam wiped his mouth and dumped Dean on his bed to sleep it off. They could talk in the morning. When Dean woke up, a hangover to add to his no doubt aching body (if Sam's was anything to go by, it still felt like Dean was inside him if he moved too fast) making pained groans leave his mouth, Sam made them both coffee and waited for Dean to join the land of the living. "Dean, we gotta talk." "No we don't." Voice rough with sleep and last nights drinking, Dean turned away from him. "I miss dad too. But I don't regret last night. If you do, I'm sorry." There was silence broken only by Sam sipping his coffee and Dean noisily slurping his for a few minutes, then Dean's near inaudible whisper of "I don't either." Relief flooded Sam for a moment, glad one night of madness hadn't cost him his brother.

They didn't talk about it much from then on, sex was just another part of their life as they went. Losing Dean to that demon deal had torn a hole in Sam, one he filled with demon blood and Ruby and darkness. The first chance they got was spent frantically reconnecting, and neither of them could walk straight the next day. If Bobby suspected something, he had never said. Then Castiel had come along, talking about seals and Lilith and Lucifer. The brothers fell out over Ruby, the demon blood and a hundred other things. It always resolved itself the same way, harsh and rough sex followed by drunken words of forgiveness. Along the lines somewhere, probably half down to whiskey, Sam had convinced Dean to put on makeup again. Dean was hesitant, saying he didn't want Sam seeing him as a girl. "You're all man Dean, I just want to see." That night had probably been some of the best sex they had ever had, and it only got better as Dean let Sam push it further. It wasn't about Dean being "weak" or "inferior", he just looked hot as hellfire and Sam loved it. They had tried Sam in makeup and lace, but both admitted they preferred it on Dean.

Dragging himself away from nostalgic memories, the bathroom door opened. Dean stepped out, a black dress with a green shimmer in the light straining across the broad musculature of Dean's chest and shoulders. His perfect cheekbones and nose needed no help, but a light layer of mascara turned Dean's already sweeping, long eyelashes into works of art framing those perfect green eyes. Lip gloss enchanted his mouth, the near-pouting lips sparkling like a beacon Sam needed to answer. There was a faint glitter around his eyelids, just enough to draw a little more attention to his beautiful eyes. "How's this Sammy?" "Perfect. Get here then! Cas wanted a demonstration after all." Dean slinked over to the bed, stradding Sam's hips and leaning down to kiss him. Hands slid under the dress, cupping Dean's ass and feeling the lace material. Dean's cock strained at the front, leaking when Sam wrapped a hand around the stiff length.

Truth be told, Sam would have forgotten Castiel was even there if he hadn't moved, sitting on the other bed to get a better view of the brothers. The angels pupils were dilated, tongue peeking out to lick chapped, dry lips though Sam didn't think he knew he was doing it. The brothers shared a smirk, silently agreeing to keep pushing the angel, to see how far he could go just watching. Resuming their kissing and groping, Sam could feel slick moisture between Dean's ass cleft. "Oh, I'm all wet and ready for you baby brother." Groaning and thrusting his hips upwards, Sam realised what the click he had heard was - lubricant. "Fuck Dean, you're perfect you know that?" Dean rolled his hips, grinding their erect cocks together and even through his jeans and Dean's layers, Sam groaned at the feeling. Hands tugged at his zipper, fumbling and rearranging limbs to get the denim down and out of their way. The impeding fabric gone, Sam's cock sprung up between them, pulsing to get inside Dean.

There was a scramble for the tube of lube Dean always put in his bedside table in every motel, right next to the bible that almost every motel had. Sliding lubricated palms together over Sam's cock, he grunted at the teasing pleasure until Dean deemed him wet enough. The next fumbling was to push up the skirt of Dean's dress, separating just long enough to pull away the lacy underwear before Dean was straddling his lap again. They shuddered simultaneously as Dean lowered himself, sinking down Sam's erection with relative ease until they were flush against each other. He let Dean set the rhythm, thrusting up as Dean dropped down and rubbing his thumb over Dean's shaft to stimulate him inside and out. Confusion sparked when Dean stopped, flicking eyes over at Cas. Sam raised an eyebrow to say "are you sure?" and Dean nodded, smirking darkly. Sam nodded in reponse, looking over and finding an unmistakable bulge tenting Castiels trousers.

"Hey, Cas. You want to get in on this?" The angel jumped, as though he had forgotten they could even see him. "I beg your pardon?" "You. Sexual intercourse. Now. With us?" Fighting not to just fuck into Dean with abandon as it was, there was an undeniable allure to them truly pushing Cas past normal angel limits. And the vessel he wore was not unattractive either. "I... I don't know how." "Well for starters, lose the clothes." Barely a second after Dean spoke, Cas was naked. Slender, lean muscles and a respectably sized erection filled Sam's vision, though Cas didn't seem to understand. "Now come kneel behind Dean, and get a handful of this on your cock." Cas took the tube, kneeling behind Dean, and Sam had to bite back a laugh as Castiel jumped in surprise when he lubed his erection. "Is it supposed to feel... Strange?" "Its good, you'll get used to it. Now, line your cock up with Sammy here and push in. Slow and easy Cas, it's not rocket science." Cas was hesitant but complied, and Sam made himself stay still, stroking Dean's cock just enough to distract from what must be wicked on the nerves as he was stretched wider.

"That's it angel boy, now stay like that for a minute." Dean writhed between them, adjusting to the extra pressure. After a few minutes of Sam still rubbing at his erection, Dean nodded and rocked his hips. "Now Cas, move your hips so you kind of pull out, but not all the way." Dean had likely just taken an angel of heaven's virginity, but nobody seemed to notice as Cas followed instructions, the gravelly deep voice intoning grunts and groans as his body took over instinctively. "He's got it Sammy, feel free to join in any time." Thrusting up sharply for Dean's cheek, Sam did indeed join in, sliding up and down in opposition to Cas so Dean was torn between one or the other filling him, and the feel of a hard cock sliding against his own while inside Dean was frankly amazing, and Sam wished he hadn't wasted years of his life never knowing it. Now the initial pain of entry was fading, Dean was more active than either of them, rocking and bouncing between them for more stimulation. "Come on you two, what's it take to get fucked properly round here?"

Castiel more than rose to the occasion, a faint white glow behind his eyes making Sam worry for a second but Dean was practically coming on the spot as the angel let loose, thrusting hard and fast into Dean until he spilled between their bodies, shaking all over and whimpering as Sam and Cas both thrusted up and came deep inside him. "Wow, that was... Heavenly." Dean couldn't resist making dumb puns when his voice came back, clearly. Castiel took a minute to clock on what he was supposed to do next, pulling out of Dean and stepping back. "I am... Sticky." "Join the club feathers, sex is meant to be good and messy." Dean carefully lifted off Sam, hissing in pain and laying down next to him. "You ok big brother?" "Just a little roughed up, I can handle it. Your ass is mine next time though." "Is it a Rota? Mandatory turn taking?" "Not for everyone Cas, but with us it's pretty even." "Does that mean I get to dress up?" Sam and Dean looked at each other in surprise before sharing a grin. "You can play dress up if you like Cas."

-SPN-

 **To clarify, bottom boys are champs for taking it, if anything I feel a little bit of a wimp for not being able to take it without feeling like I fell down the stairs the next day! But this was all a bit of fun. Enjoy!**


	2. Cas

**Requested by r** **aelle23. Here we have Dress Up part 2 - Cas gets cute!**

 **If you read the first part and still need warnings, you may want to check Naomi didn't scrub your brain clean. However, I'll do them anyway.**

 **Incest, cross dressing, double penetration, group/threesome etc, full and flagrant disregard for the purity of an angel... Oh, and unprotected sex, which I actually don't condone in reality because condoms are good but for the sake of fanfiction lets play pretend.**

 **There's some just plain ol' Wincest to start with, the good stuffs further down because it took me a while to get back into writing these characters - I write so much Young Dracula I almost wrote 'Vlad' multiple times.**

-SPN-

"Dean, what the hell are we doing?"

"You heard Cas. Our fallen angel wants a dress."

Sam, who still struggled with the whole 'touched by an angel' thing since Cas' last visit, when Sam had been the one to bottom for the angel - not him and Dean together, they were on a hunt, he needed to be able to walk - and he realised they had literally defiled a vessel of heaven, shook his head.

"I'm thinking blue, bring out those eyes."

Dean had no such concern, though he was careful not to mention gender in the dress store they were in. It wasn't a conservative state, but two guys talking about buying a third a dress? Kinda weird, they were trying not to raise too many eyebrows. They still had to go makeup shopping yet - Dean was running low, and Cas may not suit their current collection.

"Whatever you think Dean, let's just get a move on. I'm hungry, and it is usually you who says that."

"Can't rush these things Sammy!"

Rolling his eyes, Sam perused the store quickly, hoping he would spot something suitable, they would buy it and find somewhere that sold a half decent salad, or at least a sandwich not coated in grease. His eyes landed on one, midnight blue and probably just above knee-length for Cas, with thin straps and - when he headed over to it - soft to the touch.

"Dean?"

Sam held it up, and Dean's eyes went dark as soon as he saw it.

"Perfect. Now for the matching underwear. Do you think Cas would prefer a thong or briefs?"

Sam closed his eyes, counted to ten and reminded himself Dean didn't put out when he punched him in the face.

"If you ask that any louder God himself will hear you!"

Dean was unapologetic, garnering several amused and confused glances from other shoppers. Sam didn't know if Cas even _wore_ underwear - he undressed with angel mojo. And there was no criteria list for cross-dressing a heavenly host. All the same, he felt his cheeks heat a little when Dean held up a pair of snug lace briefs in powder blue, picturing Cas' pale thighs with those riding along the top.

"Bingo."

Food forgotten, Sam barely waited for Dean to swagger to the counter and buy the damned things before they were in the car, swinging the Impala into the motel car park at probably dangerous speed. That cheeky smirk across Dean's face told Sam he knew damn well what was going on in his head, which meant he was on board. A good thing really, because Sam had them both naked and lubed fingers buried inside Dean in under five minutes.

"Damn Sammy, this really brings out your fun side."

Their mouths mashed together roughly as Sam fucked into Dean's willing body, grunting and sweating like animals and Sam _loved_ it. Loved Dean's thick cock rubbing and leaking against his abs, loved the half-lidded lustful stares beneath long eyelashes as Dean lost himself in the feeling. Hurried and rough, explosive and hot, Sam shuddered through his climax as Dean spilled, sticky and copious with a deep, erotic groan.

"Sammy?"

Muscles lax as he lay on his stomach, ignoring that his stomach was covered in Dean's come which would _ruin_ the bedspread, Sam lifted his head and glanced through sweaty bangs.

"Yeah?"

"We still gotta go makeup shopping."

He could only groan weakly, leaning over to nip at the muscular shoulder that was in range and feeling the familiar heat in his stomach when Dean smirked.

A quick shower that ranged the full spectrum from arctic to hellfire in ten minutes later, the two were out hunting for a twenty-four hour diner, Sam now ravenously hungry after their... activities that delayed eating. The diner they found did nothing healthier than some overly dry scrambled eggs, so Sam relented and got a 'real meal', thick cut potato wedges, cheeseburger and the tallest coffee they made twice. He smirked to himself when Dean sat himself down a little delicately before devouring two bacon cheeseburgers - and stole half of Sam's side dish.

"I am stuffed. We gotta come back here again tomorrow when I don't look pregnant."

Dean paid, Sam added the tip and their bill had the waitresses phone number on. It was impossible to tell who for as she smiled at them both in a sickly sweet, flirtatious manner, but they weren't all that interested anyway. Dean smiled and pocketed it to be polite, then complained when they left they couldn't go back without it being awkward.

"If you stop complaining, I'll buy you a pie from that bakery when we drive to Sioux Falls tomorrow night. Now come on, that ghost won't gank itself and you've distracted me enough."

Fairly sure Dean only heard "pie", they slid neatly into the front seat of the Impala, stopped off at a late-night store for salt, beer and 'road snacks', Dean tossed a bottle of lube into the basket which made the teenage boy server blush so hard Sam thought he might die, they were on their way.

The ghost was an easy hunt, because they had already twigged the body was cremated and tore the abandoned house apart for remains. Watching the bloodied towel from beneath the floorboards go up in flames, Sam grinned.

"Right. Back to the motel, get my four hours, go buy Cas some mascara, get gas and then we can get going to the pie... I mean job."

They tossed the ruined topsheet off, crawled beneath the surprisingly cosy blankets together and slept like the dead. Sam was always the big spoon, regardless of who fucked who, because Sam's longer legs meant Dean's knees pressed uncomfortably into the back of his thighs if Dean spooned him. Dreams of Cas and a lingerie store meant Sam was achingly hard when he woke, rutting for friction against Dean's lower back before he was even conscious.

"No way are you topping again after last night. Man that was great. Roll over Sammy boy!"

Dean straddled his thighs when he had Sam lay on his front, drizzling the tingly-lube that drove him wild along his crack, teasing and just a little too cold for sleep warm skin. Sam wriggled and squirmed, feeling Dean's cock nudge between his cheeks and cursing that he _always_ needed stretching and loosening when they did this, because his narrower hips made him tight and Dean's girth was almost too much anyway.

"Don't worry little bro, I'm gonna fuck you good."

Whining needily, Sam felt rough, calloused fingers rub the lube in, tingling along the sensitive nerves there until Sam could hardly breathe. _Finally_ there were fingers inside him, working him open with practiced ease and the edge of tenderness Dean's touch always had like this, no matter how feral the fuck Dean would always do this part right, keep it up until Sam was sobbing, begging to be fucked.

"Ready for me Sammy?"

"Do it Dean. Fuck me, please!"

A little cliche, Sam had to bite the pillow to muffle his screaming when Dean finally penetrated him properly, lest he wake the entire motel and alert them to the fact his brother was about to fuck him, and oh wasn't that brilliant. Morning breath meant they couldn't kiss yet, but Dean peppered kisses along his shoulders, rolling his hips slow and deep to make sure he was ready to take it properly.

The slow, burning ache was amazing, the drag along his prostate with each push-pull thrust enough to make him see stars. Dean's stocky hips came flush to his ass each time, sliding home deep with each thrust until Sam was thrashing, cursing his lack of leverage to push back and whining, begging for more.

Never one to disappoint, Dean delivered brilliantly as he sped up, their lazy morning fuck a race to the finish line now, the tantalising friction between rough sheets and Sam's own stomach pushing his cock to spurt, a warm puddle spreading beneath him and the clamping of his muscles dragging Dean along with him as heat flooded his insides.

Ragged panting was the only sound for several minutes, then Sam's mild gasp of discomfort as Dean slipped free. Dean seemed to have a second wind already, slapping a broad hand on Sam's ass and laughing aloud when Sam reached behind to swat at him.

"Rise and shine Sammy! Pie!"

Cursing Dean to every deity his post-coital brain could come up with, Sam staggered to his feet and crawled under the shower, which had him alert in no time when it turned freezing cold and even Dean shrieked in surprise.

They found a different diner with a great breakfast menu, and Sam could happily have eaten a dozen of his cheese and spinach omelettes but settled for two, watching Dean scarf down pancakes and bacon. They ordered extra coffee to go, then it was back to their side quest - corrupting Castiel.

"You don't use blue eyeshadow for blue eyes!"

"It'll match the dress."

Ignoring the fact they were having possibly the campest conversation they had ever had - including the merits of strawberry vs blueberry scented moisturiser - Sam wasn't sure _where_ Dean had learnt the next phrase he came out with.

"You don't display sapphires on a blue cushion!"

He couldn't help laughing, just a little, at the dumbstruck expression on Dean's face at the words that had come out of his own mouth. They eventually agreed on a 'smokey eyes' pallette, and Sam got the honour of picking out a lipgloss and mascara that he thought would suit Cas, while Dean 'treated himself' to some new things - they were ditching the cards they had on them that night, he was making the most of it.

Plus, Sam would undoubtedly benefit from whatever Dean purchased.

Rather than lip gloss, he found a moisturizing, fruity flavoured (according to the packaging) tint-lip balm, remembering Cas' chapped lips because the angel didn't need to drink. Pretty Cas should have a softer mouth to kiss and fuck. The angels lashes were already jet black like his scruff, and the soft little hairs that circled his nipples, so Sam went for something that was supposed to add 'volume and length' rather than a heavy black tint they didn't need.

When had he become such a makeup expert again?

The middle aged woman who rang up their purchases (Sam saw Dean had found protein bars in the diet section of this department store - they looked plain and nondescript next to the array of glittery, pretty things) seemed very surprised at the two stereotypical macho men dropped a basket full of beauty products on the counter, but they both smiled a little vacantly until she was done.

"I always forget how funny that is, like two good looking guys like us couldn't have girlfriends."

"I don't know man, she probably heard your sapphire comment."

"Shut up. I think it was the 'anal glide' that really did it."

"Or the baby lotion."

"Possibly the fact I bought three different glosses just for me."

Unable to maintain the fake-serious faces and busting into full out belly-laughter then, they sat chortling in the Impala seat for several minutes before composing themselves. A little. Sam tossed Dean a protein bar, unwrapping one for himself and taking a bite. Used to the plain, boring or chemical-chocolate taste, the sweet taste and slightly fruity scent confused him.

"What is this?"

"I don't know, they do all sorts of flavoured these days. I think this is banoffee pie."

Uncouth as ever, Dean grinned with his mouth full, displaying sticky oats all over his teeth. Sometimes, Sam wondered how he ever thought Dean attractive. Then he caught sight of the bags they hadn't loaded into the trunk yet, and his heart rate picked up just thinking about its contents.

He made good on the promise to buy Dean a pie, and the two had an intense, drawn out night where Dean tested out the multiple new products he had, keeping his gun nearby to "masculinise the whole experience" just in case Sam suddenly decided he was less of a man for it.

They dropped in on Jody Mills, enjoying a rare home cooked meal, beheaded half a dozen vampires together at just after dawn, then went back and crashed in their motel, too exhausted to do more than wash off vamp-juice before they hit the sack. It was nearly nightfall when they emerged from the bedcovers, ravenous as they microwaved leftover chicken and potatoes from Jody in tupperware.

"Chicken not shaped like a burger or nugget. Now that is novelty."

"You realise how weird our lives are that that even makes sense?"

Dean burped into the back of his hand, grinned and popped open a beer. Sam followed suit, feeling the beginnings of a pleasant buzz after the second.

"Now?"

Sam knew Dean had been just as interested in this as he was, waiting for them to have finished 'shopping' and have a night off but they both **really** wanted Cas back in their sex life. Not because they had tired of each other, it was anything but that - Sam got to enjoy Dean's kink for dressing up, but Dean had yet to really be on the other end of it since they agreed it didn't suit Sam. Plus, Cas was _hot,_ they both agreed that so why not enjoy it?

"Let's get all his stuff out, so it's good to go."

Having gotten a room with two beds for a change - it was all the motel had available - they laid Cas' 'outfit' out on the spare bed. Sam dropped the baby lotion and lubricant into the bedside drawer - they didn't need it yet - and changed into clean jeans and shirt, no underwear. Dean did the same, then rolled his eyes when Sam indicated he should do the praying.

He couldn't deny, there was something that went straight to his cock about Dean praying to an _angel_ so they could perform all sorts of dark and dirty depravities to him, near him, with him. The soft sound of wingbeats later, Castiel was in their room, the usual half smile they got instead of total vacancy ever since they had gotten intimate with the angel across his face.

"Hello Dean. Sam."

"Cas! We got you a gift."

"But Dean, I'm an angel. I require no material mmmph."

Sometimes the only way to shut Cas up was to kiss him, and Dean took that job on quite happily, teasing with his tongue until they knew Cas was more on their wavelength than before.

"Look."

Cas, eyes a little glazed now, turned to the bed, pupils dilating as he took in the ensemble waiting for him.

"So, Cas" Sam could see the effort it cost him to tear eyes away from the untouched clothing "wanna play dress up?"

He hadn't considered it until now, when Cas 'popped' out of his clothes and they heard him land in the bathroom, 'his' things disappearing with him, but he wasn't sure Cas would know what to do with the make-up. He didn't even have a normal face in heaven. He beckoned Dean closer, whispering into his ear.

"Don't laugh if he doesn't get the make-up quite right, he's new at this remember?"

Dean nodded shortly in understanding, then claimed Sam's mouth in a blistering kiss as the reality of what was coming began to hit them both, stripping out of their shirts as blood began to heat.

"Don't get carried away, tonight is about Cas."

They heard a mumbled curse and rattling plastic, and Sam could just picture a perturbed angel dropping the cap of his tube of balm or knocking eyeshadow all over the floor. Arousal began to ratchet up several notches as silence fell, and his heart hammered in anticipation when the door finally opened.

"Damn Cas, you look... wow."

Far from clumsy, his face was perfectly done. The habitual stubble waa gone, but he hadn't been gone long enough to shave so he guessed the angel could just pop it off. A touch of black eyeshadow was shimmering across his cheeks, highlighting his cheekbones and the gorgeous mix of silver, grey and black blended over his eyelids was amazing. A line of kohl beneath made his 'sapphires' pop even more, the hint of colour from his lip balm turning a chapped half smile into a soft, inviting pout. Mascara, lightly applied just right, meant that his eyelashes brushed the peaks of his cheekbones with each slow, calculated blink.

And the dress. Oh, the dress. Even without the usual breasts or hips that were often required to fill out such a garment properly, that slice of night sky was _made_ for Castiel. It swished lightly just above his knees, the dusting of black hair over his shins not even registering. The colour highlighted his eyes even more, and Sam decided he would go to hell for defiling an angel happily, because it looked like **that**.

Sam was pretty sure he had forgotten how to breathe at some point, and when he managed to look at Dean, the exact same expression was mirrored on his brothers face.

"Did I do it correctly? I only watched three dozen instructional videos for this strange glittery substance, there were thousands more but I did not want to miss your call."

Blimey, Cas had _studied_ how to put on eyeshadow. That was above and beyond, showed just how much the angel had been invested in this moment.

"You... Damnit Cas, I don't have words. Get over here!"

They pushed Cas to lie between them on the bed, taking turns to kiss the painted lips and caress the smooth fabric. He made appreciative little sounds, squirming happily between them. Sam leaned over for the bottle of lotion, both he and Dean backing up. Cas looked most perturbed, until they manoeuvred him to lie a little more like a starfish, Sam drizzling lotion along one arm and leg his side, then handing it over to Dean.

"We don't always go for moisturiser, but you look so hot this is a special occasion."

The lotion was chosen because it had the 'powdery cotton' scent - to most, it meant babies. To a hunter, it meant a first aid kit that didn't involve using their own clothes for bandages. Cas lay there while they worked it into his skin, massaging and kneading, tracing swirls in the slightly dampened hair across his legs before working his dress up, Sam desperate to see the briefs that had haunted his dreams since they bought them.

He wasn't disappointed. Stretched thin over the tip of his hard cock, a damp patch darkening the fabric and they cupped the curve of his ass so well Sam wanted to burn that image into his retinas for at least a year, just to savour it.

Skin soft and smooth here along his inner thighs, Cas wriggled at the ticklish sensations where their fingers traced up and down, still new to sex itself but a quick learner, pushing down to try and get their hands higher up. Years of working as a twosome, a team, meant Sam and Dean had no trouble co-ordinating their efforts as they taunted the angel.

"Is this torture-ah" Cas gasped, and it was a beautiful sound as a hand finally wrapped around his leaking erection "customary?"

"Not torture Cas. Foreplay. Sometimes, you just gotta take your time."

Sam palmed his cock while Dean kissed him, and Cas was wide eyed, sweating a little already and the strap on his left shoulder had slid down already. Coupled with his dress hiked up around his hips, the slightly smeared colour across his lips and the growing dampness of his briefs, he looked thoroughly debauched and they weren't even _started_ yet.

"You want the back or the front?"

It was a painfully difficult choice, but Sam mused they could always do this again and trade places.

"Back. Your mouth was made for oral Dean."

He got a hint of a smirk, but didn't stop to enjoy it too much as he reached for the lubricant, feeling Cas quiver between them as they hoisted him up between their kneeling positions, sliding the briefs down just enough to access his sensitive areas better, but not so much Sam couldn't still feel them.

"It might feel strange, but we promise"

"You're gonna feel so good when we're done."

Cas hadn't bottomed yet, they had wanted to save it for this, give him the full experience. Snapping the lid open and trying to warm the slick oily substance between his fingers, Sam waited for a sign Cas had even heard them.

"My vessel is sturdier than yours, I am not concerned."

Figuring that was Cas-talk for "I trust you", Sam gently probed between his cheeks, _loving_ the needy whine Cas made when he rubbed lube into his tight muscles, relaxing it slowly. He kept eye contact with Dean until they shared a nod, and Dean dropped down to seal his mouth around Cas' cock, timing it perfectly with Sam slipping a finger inside. The entire motel room rattled a little when Cas groaned, reaching to fist Dean's hair and grip Sam's arm for purchase when they hit him with dual sensations.

The soft fabric of the dress kept rubbing tantalisingly across Sam's bare chest, and he was surprised he hadn't torn a hole in his trousers for how hard he had been since they started, but tonight was about Cas. He could wait. Maybe.

Cas clenched around his finger, reminding Sam he had slowed down too much and hurried to rectify it, spreading lube around and feeling the tight muscles start to relax. Adding a little more lube, he pushed back in with two and sought the hidden treasure. The angle was difficult, but when his knuckles brushed against the right spot he heard Dean gag as Cas' hips jerked suddenly.

"Found it."

"What, my lungs?"

Dean's lips were swollen, reddened and wet with his saliva, making the visual of his gasping for air that much more intense as he recovered from the surprise intrusion to his throat. Instead of resuming his oral ministrations, Dean picked up the bottle from the bed, adding some to his own and sliding two fingers in alongside Sam's.

Cas whined at the sudden stretch, but Dean simply nipped at an exposed collarbone before reminding him with a husky whisper, that it was going to be a lot more to take Sam and Dean together. He saw the faint glow reflected in Dean's eyes as Cas took the challenge, and Sam felt the muscles around him loosen more than they had been.

"Did you do that Cas?"

"I'm growing impatient. And you both still have clothing on. This is not conducive."

They wriggled and grunted and Cas huffed before 'popping' their clothes off completely, trying to angle for position. Sam's legs were too long for him to kneel behind Cas without making it a very difficult angle, so he was relegated to flat on his back as Cas essentially mounted him, finally knowing the feeling of being inside an angel.

His body was a little colder than Sam or Dean, not by much but noticeable against human-furnace Dean. Cas rocked himself a few times, testing the depth and feeling before he pressed his body along Sam's, rubbing fabric against skin and staring deep into Sam's eyes for a second. Dean held up the discarded briefs with a smirk, then eyed where Sam was buried inside Cas.

"Is that my cue?"

"Yes."

The stretch must have been harrowing, but Cas took it like a champ as he felt Dean slide home next to him. Cas squeezed, moulded until he fit them like a glove and whined, long and low in his throat before spilling across Sam's stomach. They hadn't even _moved_ yet.

"I ejaculated prematurely. I apologise."

"Don't worry about it Cas, we are very good."

Unsure what they should do just yet, Sam waited for Cas to soften, come down off the edge, thighs shaking with the suppressed desire to thrust and fuck up into Cas with abandon.

"What are you two waiting for? I am perfectly capable of multiple climaxes. Move!"

Supposing they had their orders, Sam nodded up at Dean, sliding out as Dean pushed in, thrusting back up as Dean pulled out. It was a little awkward to begin with as they found their rhythm, but eventually Cas grew bored with the waiting and started rolling his hips, taking them both to the hilt over and over again.

The dress was still around the top of his thighs, his cock still jutting out beneath the fabric as it rose and fell with him, stretching out the sinfully long torso as he leant back against Dean and fucked himself on the twin impalement, lengthened lashes brushing his cheeks with every blink as Cas lost the fight to keep his eyes open under the onslaught.

For someone who was new at this, Cas certainly knew how to put on a show that could make the devil himself blush. They had been holding out for far too long now, and even with "tonight is for Cas" in his mind, Sam felt the heat of climax tear through his body, feeling Dean follow as they both pumped into Cas, seeing stars and making unholy sounds.

He could feel Cas still firm against his stomach when he clawed his way back to reality, noticed the way he was shaking all over as Sam and Dean started to soften inside him.

"P-p-put your fingers back in me."

He didn't even blink when they both pulled out, making eager, greedy sounds when they both pushed two fingers back inside his leaking hole. From this angle, Sam could reach his prostate easily, Dean's fingers undoubtedly adding pressure until Cas whimpered desperately. Dean's other hand slid under the dress, and Sam watched rapturously at every pump of his hand, sliding beneath the fabric, up and down and back again.

Cas let out the most sinfully erotic sound yet, bucking into Dean's hand and squeezing hard around their fingers, sticky and sliding easily inside him from their own come. A dark stain saturated the fabric, fluid running down and dripping over Sam's hips and thighs as the angel finally broke, then dropped heavily onto Sam's body.

Extracting their fingers didn't even make him twitch, and though angels didn't sleep Sam wasn't sure that was true when Cas stayed still, eyes closed.

"I may have stained the fabric."

The words were barely a whisper, usual gravelly voice even lower and Sam's cock gave a hearty twitch at that, a heroic effort given how spent he felt.

"Don't worry, we can get stains out of anything."

Cas eventually pushed himself upright, and Sam could see where the dress clung to his groin, perfect outline of his sticky, sated self. Dean helped the angel stand on only slightly shaky legs. There was glitter on Sam's torso from the makeup Cas still had on. And the motel owners probably thought they were making porn from all the sounds, and the fact he thought the bedsheets were unsalvagable now. At least they had a spare tonight.

Despite the fact they were so fucked out Sam thought another round might kill them, he felt heat begin to build as Dean led Cas to the bathroom, winking over at Sam.

"Next time, we can both dress up, and Sam can be in the middle."

-SPN-

 **Actually had more fun with this than I expected! Thanks for the prompt!**


	3. Skirts

**Raelle23 - I'm glad you enjoyed it! I hadn't considered skirts much to be honest, but that was good inspiration so here it is!**

 **Shannonisabanana - There is a third chapter! With both dressed up and Sam the poor victim... Well, there is now! *points down***

 **Sorry this took so long to write, but I'm shit like that!**

-SPN-

"Whatcha doing Cas?"

Dean dropped heavily into his seat, muscles aching with the werewolf hunt from hell and leaned over to see what the angel was staring so intently at.

"Browsing. Would you say I am more of an apple or pear?"

The thing in question transpired to be a fashion magazine, and the article in particular Cas was reading was all about how to "dress for your shape". They had created a monster.

"Uh, neither. You've got no curve in your hips or waist. You got a freaking great ass, but no fat on your thighs. So you are neither. Why, what are you thinking?"

Cas indicated his goal, winning a smirk from Dean as they looked over at Sam.

"I'm gonna take a quick shower, then we can go shopping. I'll get dinner on the way back Sammy!"

The first was said only to Cas, the latter called out to Sam where he was across the room, polishing his pistol.

"Where are you going?"

"To get food. And Cas wants to check something out. An hour, two tops. Anything in particular you want for dinner?"

"Not dripping in grease, otherwise too hungry to care."

The hot shower did a miracle of sorts to his tired muscles, and Cas' idea had given him a second wind - as did the promise of bacon cheeseburgers. There was beer in the motel room, so they were good on that front. Though he remembered they were low on lube... ever since Cas and the dress happened, their menage-a-trois relationship had continued to blossom with a surging heat.

"Dean, what dress size is this vessel?"

A couple of nearby patrons gave Cas sideways looks, but his strange words combined with that half-vacant not-of-this-earth expression on his face meant most were content to just ignore the strange man in a trench coat. Grinning to himself - Cas was a hoot - Dean scanned the shelves for something to his tastes.

"You're about a ten. That dress was anyway. Maybe a twelve if it's tight."

Spying a display of A-lines, he knew he was on the right track and moved in that direction. Castiel, it turned out, wanted to go one further while they were out, eyeing up some _stiletto heels_. Jesus, Dean didn't know how the world would cope if Cas' gorgeous legs got any longer... Sam was bad enough for that. He could just about fit in the largest size available in that store - Jimmy Novak had fairly small feet it seemed.

"This is a frivolous purchase."

Cas contemplated the box on his lap, a couple of bags in the back of the Impala containing all the more pleasant treats of the evening.

"So is using lube on you when you can make it yourself. Sex is a frivolous thing to you. Basically, shut your pie hole and keep the motor running."

Brow creasing, Cas leant back and watched the Impala while Dean hit the convenience store for candy bars, protein bars, the weird Greek biscuits Cas liked and a couple of bottles of lube. There was a sale on the bags of road salt now winter was easing off, so he grabbed two of those - they came in handy for ghost-proofing whole rooms at once.

"Here ya go Cas!"

"I am an angel, I don't need to eat."

"I once saw you eat three hundred cheeseburgers. You like those."

A small smile fixed itself on Cas' face, and the little honey covered crunchy things disappeared one by one into the angels mouth between the convenience store, the diner and then finally the motel room.

Sam noticed when he kissed them in greeting - Dean first, then Cas. He licked his lips, tasting the sweet confectionary.

"You been treating our angel?"

"Oh, you have no idea Sammy boy. Soups on."

Sam handed him an opened beer, Dean handed back a cheeseburger with all the salad, sweet potato fries and some flavoured water thing.

"Wow. Almost _healthy._ What's the occasion?"

"Cas and me want you to have your strength back for tomorrow is all. We got a surprise but you're too beat up. Plus it's getting late and we've done the job but we're paid through til Friday. So eat up, sleep up and get ready."

The anticipation may well have almost killed all of them... ok, maybe he was being a tad overdramatic. A good nights sleep and breakfast Sam went out to get later, both Winchester brothers were feeling a whole lot better. Dean sent Sam to shower while he and Cas got 'ready', knowing there would be a near instantaneous reaction from him when he exited the bathroom.

"I think this garment may be too small."

Cas looked perturbed by the fabric that barely stretched across his ass, only just long enough to disguise his cock at the minute. Dean hadn't realised it was _quite_ that short himself.

"Nah, it's meant to be like that. You bought a mini-skirt Cas. Come on, get the shoes on before Sam comes out!"

A new sort of bonding for the two had been that they now took turns doing the others make-up - sometimes with Sam watching, because he would get hard just watching the accentuating of features, the delicate dusting of colour and shimmer across usually textbook-masculine-strong faces.

Cas had even learnt not to jab Dean in the eye with the mascara wand. Checking his reflection in the black screen of his phone, Dean pouted at himself to check the sheen of his lip gloss.

"Yeah, I'd do me."

Testing himself in the stilettos, Cas was naturally graceful as an angel and the effect they had on his legs was literally mind-blowing. Dean felt the slim green skirt he had on tighten, aroused by the miles-long legs extending from the navy mini that currently barely hid a thing.

"I'd do you too, damn Cas. But today... today is all about torturing Sammy."

The shower shut off, and Cas still being _Cas_ sat down, crossing his legs awkwardly which only served to make his barely-there skirt ride up higher, revealing the edges powder blue briefs that drove Sam crazy with their lace detail.

Dean could detect the sounds of Sam having to roughly towel dry his long hair, then comb it through to prevent it being a chaotic explosion as it dried. Sure enough, there was a couple of muffled swear words where he came across knots, because they didn't always have _conditioner_ to hand on the road.

Eventually the door opened with a cloud of steam billowing out, Sam in nothing but a towel appearing like a beautiful apparition in its midst. There were stray water droplets rolling down his gorgeous bronze chest muscles, leading down the firm stomach to be halted by the impeding towel. Raking his eyes back up, Dean finds the damp hair drying at the ends already and settling around his broad shoulders.

"Wow. Cas was **made** for heels."

"Right? You gonna stand and stare or what little brother?"

He crossed the small room in two loping strides and dove in to kiss Dean, mapping the bare torso that led to the slim fitting skirt.

"I think we found your new hunting outfit."

"In your dreams Sammy. We would never get anything done."

His mouth tipped up in a smirk, then Sam turned to kiss Cas deeply too. The angel tipped his head back, letting Sam ravage his mouth repeatedly while Dean enjoyed the view. Inhumanly strong, Cas pinned Sam down on the bed beneath him and the tangle of impossibly long legs, gasping sounds and Cas' pert little ass peeking out from under his skirt had Dean wanting to abandon the 'plan' there and then.

"Damn, it's hard to believe you were so innocent a year ago Cas. I think Dean's a little lonely though, and today was his idea."

Cas twisted his head around, observing Dean with his big blue eyes and offering position.

"You are correct. He does look lonely."

"How do you want us Dean?"

Pulling Cas to stand up at the end of the bed, Dean manipulated Sam's endless limbs up onto his hands and knees, stripping the towel away to reveal the heavy erection jutting out from his body. The outline of Cas' cock was pressed tight against the fabric of his skirt, and when Sam spied the tempting little briefs beneath he made a needy whine.

"Don't give him what he wants too easy Cas. Make him work for it."

Sam whined again, nuzzling Cas' groin and releasing hot little mewls. Dean knelt up behind Sam, dumping lube into his hand and setting to work Sam open quick and hard. It would still hurt, still stretch just a little too much but when he was in this sort of mood, Sam _loved_ it like that. Watching ravenously, he saw Sam had managed to roll the mini up over Castiel's full cock, straining against the fabric that was rapidly dampening with a mix of precum and saliva where Sam mouthed hungrily at it.

Dean had never really been in the middle like _this_ himself, but knowing how it felt to have Cas thrust into his throat and have Sam fuck into his ass separately, he could only imagine how intense, how overwhelming it would be for Sam very soon.

Seeing Cas stare hungrily, Sam turned his head to see where Dean was lifting his skirt up, rolling the (comfortable, sue him) lace-front panties down to sit just behind his balls. That pushed them forward and gave Dean an added sensation around the sensitive area, and judging by the dilated pupils in both sets of eyes on him, it looked hot as fuck.

"C'mon guys, you're killing me here."

"Actually Sam, you are statistically more likely to die from sexual intercourse than unsatisfied..."

"Cas, shut up and give the man his treat."

Dean grinned as Cas fell silent, both Winchester brothers much used to the angel reeling off random facts that didn't improve the mood. Slicking his pulsing erection with lube, Dean paused to ensure Cas wasn't in Sam's mouth and at risk of being bitten, then pushed himself in in one slow, sure thrust. Sam keened, squeezing and pushing back on the intrusion to ensure Dean was flush to him, hips to bottom.

He pulled out, slid back in a few times, making sure Sam wasn't about to be jolted in surprise - just because Cas _could_ heal _any_ injury didn't mean they wanted to test it. When the muscles almost constricting his cock began to relax as they adjusted to the pressures, and Sam was making pretty little moans as his prostate was stimulated, he gave Cas the nod.

Sam mewled happily when the fabric finally came down, letting him take the thick erection into his mouth and he gagged a little in his haste to suck at Cas' cock. Dean smirked at Sam's easy submission, moving his hips again at last to take his own pleasure from the sublime body beneath him.

The angel fisted his hands in Sam's hair slowly, using his grip to control the motions of Sam on his cock and letting his head drop back as pleasure overcame him. Cas was naturally seductive despite his awkwardness, and the fact he never realised he did it was even hotter. Dean couldn't quite help himself, thrusting harder into Sam's tight ass as he watched Cas fuck into the hot mouth wrapped around him.

Sam became overwhelmed first, letting go of Cas to drop his head and howl out his release as the muscles around Dean contracted and spasmed tightly. Cas was too close to hold back, gripping himself and stroking three or four times before he came explosively, painting thick white stripes across Sam's shoulders and back with a deep, quiver-inducing orgasmic groan. Dean couldn't help himself, pulling out and adding to the canvas of lean, long muscles along Sam's back with his own come.

The quickest to recover, Cas righted his underwear and mini skirt, wobbling in his heels slightly as his body came down from the endorphin high. Sam was still gasping, trying to work his abused throat muscles properly but across the board, Dean knew all three of them were grinning. He reached down a hand, slapped across the taut curve of his little brothers ass and enjoyed the hypersensitive, pained moan.

"Don't worry Sammy, once you're feeling a little better me and Cas will trade places."

-SPN-

 **The biggest issue, I find, with writing these one shots is that they tend to happen when I'm really out of practice writing slash and so it always seems... sub-par.**

 **Still, I'm gonna call Dress Up done!**

 **(unless someone gives me another idea I simply _have_ to write, but I feel like it's all been covered personally)**


	4. Coat

**Silvaxus - you asked for trenchcoat, and I wrote half of this and then forgot all about it. Apologies! Hope you didn't lose all hope.**

-SPN-

"Cas, you can't wear a skirt on a hunt. It's impractical!"

"I am a celestial being, practicality means little to me."

Dean threw up his hands in defeat, leaving the angel to continue admiring his reflection clad in nothing but his trench coat and skirt. They were about to head out after a shifter, and Cas didn't want to take off the impractical outfit.

"We've created a monster."

"Worth it though Sammy."

"I can hear you both, you know."

Dean stuck his tongue out immaturely at the closed door, finished brushing his teeth and spat into the sink. Sam was done a minute later, kissed him quickly and they both headed out to find Cas no more ready than they had left him.

"Cas, seriously. Take off the skirt."

The fabric vanished before their eyes and left Cas naked save for the open coat. Dean felt his mouth go dry, but they really needed to get off on the hunt.

"Ok, now put your normal clothes on before this shifter eats someone or something."

Cas 'popped' his suit back on, face showing some petulant annoyance but they had work to do damnit. If Dean could learn to wait, so could Cas.

The hunt was exhausting but productive - the shifter had a friend, and now both of them were quite assuredly dead. None of them had the energy to do more than collapse into bed that night in their motel, and Dean had almost forgotten about the trench coat thing by the next morning. Cas popped in with bacon and eggs in to-go boxes for their breakfast, and Dean ran out to buy more coffee and gas his baby up before they moved on the next day.

Whistling as he carried the bag containing beer, potato chips, beef jerky and lube into the motel room, car keys spinning around his finger to accompany his surprisingly good mood, Dean let himself in and placed the bag on the kitchen table. He pulled the lube out to move to their travel-sex-bag, then turned around and promptly dropped it.

"This was Sam's idea."

Cas was laid out on the bed, wearing nothing but his trench coat and his newest pair of skimpy underwear in crimson - Sam's favourite colour on either of them other than the usual green or blue.

"Uhhh... yeah. Good idea."

It waa juvenile and yet unbelievably **hot** to see, some image in Dean's head where Cas would wear nothing but the coat and whip it open to reveal that slim, pale but still sexy body he had squirreled away under it. Dreams did come true it seemed.

"Told ya he liked it. I think Dean has a thing about being flashed by an angel."

"Flashed? I'm not flashing anything."

"It's a phrase Cas. Flashing the goods, meaning revealing your naked self."

"Oh."

Dean wasn't really paying attention to them talking, reaching for the tie on the trench coat. Cas looked confused as Dean pulled it out, sliding it free of the loops until it was all in his hands. Turning to Sam as an idea formed, he asked.

"Where's his tie?"

"Uh, here."

"Hold that a sec. Cas, hands."

Cas held his hands out obligingly, letting Dean use his coat tie to tie them together.

"Yeah, yeah, you can break it or zap it but I can pretend."

Still confused, but getting into it judging by the erection Dean felt pressing into the back of his thighn Cas let him push his arms up over his head still bound, then tie the navy suit tie around his face like a blindfold.

"All trussed up and pretty. _Now_ we can have some fun."

He could see Cas' serious eyebrows, creasing in the middle as Dean leant down to kiss him before moving away to strip himself. Sam took off his shirt, unzipped his jeans but stepped back and pulled up a chair, letting Dean have his moment. They hadn't really ventured into this territory before, because being tied up usually meant near death and no sight meant danger... but Cas was less concerned, knew he could angel mojo his way out of almost anything. And trusted Sam and Dean implicitly.

"I understand. One sense deprived raises other ones."

"That's it Cas. Now hush, let me play."

Down to his boxers, Dean retrieved the lube from the floor of the kitchen area before kneeling on the bed next to Cas. The trench coat was like gift wrapping, Cas exposed like Dean was unwrapping him on Christmas day. The angel on the tree... angel in his bed. Close enough.

Cas whined when Dean pinched a nipple, unable to tell exactly what was happening until hands were on him. Moving to tweak the other, he felt his own cock harden as Cas wriggled. They should have tried blindfolds before... this was _awesome._

"Don't worry Cas, gonna fuck you good."

By the time Dean finally touched the angels erection, it was hard as nails and sticky with precum. Giving him a quick squeeze, Dean teased him a little more.

"That's just _so_ bad for the fabric."

He whipped the messy fabric down slender, muscled thighs until they were completely off, leaving Cas bare save for his gift wrap and binds. He was sturdier than them, and should be used to getting fucked good and proper by now but Dean loved this part, teasing him open until he begged to be filled.

"Don't you think he's been teased enough Dean?"

Cas made agreeing sounds with Sam, pushing back on the fingers in his ass and squeezing around them to try and tempt Dean to get a move on.

"You getting in on this little bro?"

"Not Cas... he's for you. Fancy a new position?"

He caught on quick, bending at the waist to let Sam slip fingers between his cheeks and aroused enough to not care about the stretch and burn of a hurried prep. Cas was almost in tears waiting by now, lifting almost clean off the bed from one brush to his cock.

"Hips up, need to raise you a little for this to work."

Cas complied, letting Dean put a couple of cushions under his hips to raise the angel to a better angle. Dumping a handful of lube over his cock, Dean finally buried himself in the angels heavenly body. Sam followed suit, filling Dean perfectly and wrapping arms around him to keep the middle man upright as sensation almost overwhelmed him.

"Uhhh, new favourite I think."

"You say that every time."

Sam's thick, hot cock pressing on his prostate while Cas squeezed and massaged his cock with his inner muscles...

Dean was in _heaven._

"C'mon Sam, you gotta lead here."

"Thought you would never ask. Let us know if it's not working for you Cas."

Sam's first thrust knocked the wind clean out of Dean, perfect aim and powerful stretch as he pushed Dean into Cas, who was near mindless with arousal by this point as he took the impact of two built, heavy guys who knew how to fuck.

 _ **"Again."**_

He begged, feeling Sam pull back and use his grip on Dean's chest to slide him out of Cas too until just his tip remained. His punishing thrust drove them both forward again and Dean forgot how to breathe as unimaginable pleasure washed through every fibre of his body.

"Yep. Definitely new favourite."

Those were the last words Dean managed to speak, every other sound some kind of desperate, pleasured wail as Sam fucked them both - he might be using Dean as a proxy, but he was fucking Cas just as much with his hard, feral thrusts.

"So close, so close."

Cas whined beneath him, the angels cock swollen and purple against his lean stomach as he was pushed into again and again with the sheer force Sam sent rolling through all of them. Cas was still bound and blindfolded, back arching up so much it looked painful until the invisible strings holding him up snapped, climax overtaking him. Cas came and came and _came,_ making a total mess of himself, his coat, the bedsheets as he spilled and cried out like he was in agony beneath the erotic torture.

Muscles squeezed tight around Dean, three more slamming thrusts from Sam and he was gone too, nails scrabbling over Cas' lean hips and drawing blood as his back bowed, cock twitched and he came with a keening cry. Sam had been holding back, grunting and biting down on Dean's muscled shoulder as he spilled hot and copiously thick inside him. Sweaty and sticky and hopelessly exhausted before midday, the three managed to pull out from each other before falling on the sticky, messy bed.

"I think we ruined his coat."

-SPN-

 **Ugh this is short and feels disappointing but it's all I could seem to force out of my brain on trench coat Wincestiel sexing.**


End file.
